That isn't how it works. At the end of the year, if you have too much income, you have to PAY BACK up to 85% of your benefits. He could be slapped with a sizable bill come April.
That's not exactly correct. You will OWE TAXES on up to 85% of your benefits, as a single person, if you make over $25,000. Also depending on what you're doing, it might prove you're actually not disabled if it's by engaging in substantial gainful activity rather than, say, passive income from gifts or interest.
The taxation rate isn't 100% of that 85%.
According to the Social Security Administration, the payments will stop in months where you make more than is allowed:
https://www.ssa.gov/pubs/EN-05-10095.pdf
Again, you're mixing up SSI (Supplemental Security Income) with SSDI (Social Security Disability Insurance).
The rules for SSDI, according to that very pamphlet you quoted:
Trial Work Period — The trial work period allows you to test your ability to work for at least 9 months. During your trial work period, you’ll receive your full Social Security benefits, regardless of how much you’re earning — as long as you report your work, and you continue to have a disability.
And this can continue indefinitely:
In 2023, a trial work month is any month your total earnings are over $1,050. If you’re self-employed, you have a trial work month when you earn more than $1,050 (after business expenses) or work more than 80 hours in your own business. The trial work period continues until you have used 9 cumulative trial work months within a 60-month period.
With some fancy footwork you could manage to collect full SSDI benefits while having an occasional windfall month and even a rather high annual income. People do this.
The difficulty is keeping it from being considered "substantial gainful activity" that would disprove that you are even disabled at all.
There's also the other question of whether being a modern sideshow geek and having people throw pennies at you is even "work." There's certainly nothing of the sort in the Dictionary of Occupational Titles.
I hope Chris at least gets to keep most of the cash Praetor is helping him make.
Where Chris is likely to run into problems is failing to pay or even file taxes on any taxable income, because he would probably end up with at least some of the tugboat (up to 85%) being taxable.
Praetor is another person looking at substantial tax liability, and I have no idea what form you'd even fill out for "exploiting a retard" income.
One of the things that might keep Chris out of trouble is if Praetor is in fact completely taking him for a ride. I doubt that parasite would do that out of a desire to help him keep his tugboat, or is even smart enough to do that to avoid killing the golden goose, but he might just be greedy enough to do it accidentally.